JPS6084268A - Novel polyalkylpiperidine compound, manufacture and use - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a product, a process for producing the compound, and plastics stabilized with the compound.

Piperidine alkylated at the 2- and 6-positions can be used as a stabilizer for photosensitive organic powders.
I belongs to part 1 of harmful amines.

Such veridine compounds usually have a polar group at the 4-position and can be unsubstituted or substituted with a -valent group at the 1-position. West German Patent Publication No. 2,538
, No. 076 has a moat, 4 (2 replaced with 17,
Bis-piperidines are described, which consist of two 2.6.6-tetramethylpiperidines bonded to each other in the 1-position via a divalent group.

Divalent radicals used here are, in particular, alkylene radicals, alkylene radicals interrupted by ether, ester or thioether radicals, and aliphatic dicarphonyl radicals.

Compared to the monopiperidine derivatives, the bipiperidine derivatives have the advantage of generally lower volatility and of being extractable. It would therefore also be of interest to carry out molecular enlargement by reacting polyargylpiperidines with un1tt substitution in position 1 with diisocyanates (or triisocyanates). However, it is known that it is very difficult to carry out carbamylation at the 1-position with sterically hindered piperidine. That is, according to Example 87 of West Germany Patent Publication No. 2,258,752, 80% pure product is 2.
2,6. ．． It is only obtained by reacting 6-tetramethylpiperidin-4-ol with excess methyl isocyanate in boiling benzene for 24 hours. On the other hand, according to Example 45 of the same publication, the reaction between 1-Ia-substituted tetramethylpiperidin-4-ol and methyl isocyanate proceeds without any problems.

From this it can be concluded that the carbamylation of the sterically hindered piperidine nitrogen proceeds very slowly and incompletely, so that there is no chance of obtaining pure bis-piperidine compounds by reaction with diisocyanates.

West German Patent Publication No. 2,834. ．． d, 4 in Publication No. 155
-The reaction of spiro-oxacilone-polyalkyl biverizines with diincyanates is described. This reaction occurs only with oxazolidone nitrogen and not with piperidine nitrogen; thus, a noticeable amount of 1-carbamyl product was produced under the reaction conditions described in the above publication (15 hours in boiling toluene). ) could not be obtained below.

Therefore, an almost quantitative amount of the corresponding bis-tris-1-carbamylpiperidine occurs within a short time when the 1-unionized polyalkylpiperidine derivative and a diisocyanate or triisocyanate are reacted at room temperature. It was surprising to find that 1-carbamylation, which does not proceed or proceeds incompletely by 1/75, under heating, contrary to all expectations, does not proceed at low temperatures. It proceeds rapidly and in high yields, and such bis- and tris-1-carbamylpiperidines have been obtained for the first time by this method of preparation.

Therefore, the present invention provides the following formula: OR, 5%-CO01
t6,-CH2C00I(,6,-Cl-12CN,
-CN, -N (R')2, -Co-N (lL
'a)2,-CH2C)(,,N (11,7),,,
-N (TL7”)'-CO-13', -0-CO
-11,9, -0C112CH2-CN.

JJ (l(,?a) -(at(1-0-R,IOl
-(1-CO-0-11,10, -0-Co -N
(n, 7a) 21 ”, - is a certain ゛ and 几3 represents a hydrogen atom, or R2 and R3 together represent O=, NC-CH= or the following formula ■, II
II IV V ■ represents a group represented by R4 is an aliphatic, cycloaliphatic, aromatic or aromatic-aliphatic diincyanate or n-
represents a valent group, ]t5 is an alkyl group having 1 to 12 carbon atoms, an oxaalkyl group having 3 to 14 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a propalkyl group, a benzyl group or -(CH2CH20 ) represents a H group (in the group, p represents a number from 1 to 10), and IL6 is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, or an alkenyl group having 3 to 5 carbon atoms; cycloalkyl group having 5 to 8 carbon atoms, aryl group having 6 carbon atoms, aryl group having 18 to 10 carbon atoms, alkylaryl group having 712 carbon atoms, phenyl group having eV to 12 carbon atoms A
・Kyl-X or formula ■: represents a negative group represented by, R7 is an alkyl group having 1 to 1B carbon atoms, an oxaalkyl group having 2 to 14 carbon atoms, an alkenyl group having 3 to 5 carbon atoms. Cycloalkyl having 5 to 8 carbon atoms, phenylalkyl having 7 to 12 carbon atoms, aryl having 6 to 710 carbon atoms, hydroxyalkyl having 2 to 4 carbon atoms if still carbon a
7&1710 represents a cycloalkyl-alkyl group, or the two R7 groups together with the nitrogen atom to which they are bonded 17 represent a 5- to 7-membered ring, and 7a represents a hydrogen atom Or lj, has one meaning of 7, 1 (1B is an alkyl group having 1 to 12 carbon atoms, an oxaalkyl group having 3 to 14 carbon atoms, -COOT-
1 also refers to an alkyl group having 2 to 14 carbon atoms substituted with 1 to 000 (alkyl group having 1 to t carbon atoms), an alkenyl group having 2 to 5 carbon atoms, an alkenyl group having 5 to 8 carbon atoms cycloalkyl group, having 7 to 1 carbon atoms
Both phenylalkyl in 2 represent an aryl group having 6 to 10 carbon atoms or an alkylaryl group having 7 to 17 carbon atoms, 1 (, 9 is an alkyl group having 1 to 18 carbon atoms, 3 to 14 carbon atoms Oxaalkyl group, -C00)1
or a C2-C14 alkyl group substituted with -C00 (C1-C4 alkyl group),
Alkenyl having 2 to 5 carbon atoms, cycloalkyl having 5 to 1,8 carbon atoms, 6 to 10 carbon atoms
an aryl group having 7 to 12 carbon atoms, a phenylalkyl group having 7 to 12 carbon atoms, and an alkylaryl group having 7 to 12 carbon atoms. also represents phenyl substituted with OH and 1 to 3 C1-C4 alkyl groups +, <K represents a 1210 phenylargyl group having 7 to 7 carbon atoms, 1 (10 is 1 to 1 carbon atom) 1'L'' represents a hydrogen atom or represents an alkyl group having 1 to 8 carbon atoms, 1412 represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloargyl group having 5 to 8 carbon atoms or a benzyl group, and 1113 represents an alkyl group having 1 to 8 carbon atoms; 12 alkyl group, cycloalkyl group having 5 to 8 carbon atoms represents phenyl group, or I
'L' 2 and J113 represent a cycloalkane or alkylcycloalkane ring having 6 to 14 carbon atoms formed together with the carbon atom to which they are bonded.
7. R1I4 is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, a hydroxyalkyl group having 2 to 4 carbon atoms; , 2 to 10 carbon atoms
an alkanoyl group, a benzoyl group, a C7-C12 alkyl group or a RN)(-CO- group, in which 11. represents a C1-C8 alkyl group or a phenyl group. )(, Is is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a hydroxyalkyl group having 2 to 4 carbon atoms, or a hydroxyalkyl group having 5 carbon atoms.
cycloalkyl group having 1 to 8 carbon atoms, 1 to 12 carbon atoms
17. Covered with a phenylalkyl group or a glycidyl group.
1716 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; I2. 1L17i, i hydrogen atom, methyl group, ethyl A, hydroxymethyl group 17, so I7 te 1 (, l B
represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an allyl group, a benzyl group, an acetyl group, or an acryloyl group. ).

Cargo group in formula ■1)・1, Bs, R6, R,? ,R
,8,■(,14(,10,R,■,l(,12,](
,lI3,l(,+4,l(,l 5,n+16is-
YobiT? , 18 F, - can be an alkyl group, and it can be a [platinum- or branched 17 alkyl group;

Examples of such alkyl groups within the defined range of carbon atoms are methyl, ethyl/n-propyl, inopropyl, nibutyl, n-butyl, tert-butyl, isoamyl, n-hexyl group; 2-ethylbutyl group, inhebutyl group, n-octyl group, 2-ethylhexyl group, n-nonyl group, isodecyl group, S, S, 5.5
-tetramethylbekful group, n-dodecyl group, n-tetradecyl group, n-hexadecyl group and low octadecyl group.

hydroxyalkyl i](, I7, R14 and)(
, +5 are 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl and 2-hydroxybutyl. Oxaalkyl group R5
, Rp, 'Hs and +1,9 are monooxaalkyl groups or polyoxaalkyl groups, such as 2-ethoxyethyl group, 2-impropoxyethyl group, butoxymethyl group, 2-hexyloxyethyl group, 3.6- Thioxaheptyl group, 3゜6-thioxadecyl group, 3,6.9-
), lJ oxadecyl group or 3-dodecyloxyprobyl group. The oxaalkyl group J(, +7 can also be a methoxymethyl group.

Possible examples of C2 -C14 alkyl substituted by -COOH or -coo (C1 -C4 alkyl) and 11,9 are 2-carbonyl, 2-methoxy, carbonylbutyl group, 2-
They are ethoxycarbonyl-decyl group, 2-carboxy-tetradecyl group and 2-impropoxycarbonyl-tetradecyl group.

Alkenyl group FL5.1(7, l(, IQ , [(, +
Possible examples of 4 and ](, 15 are methallyl group, 2-
Butenyl and 2-methyl-2-butenyl groups, allyl groups, are preferred. Alkenyl groups R.8 and R
-9 can also be a 1, vinyl, 1-methylvinyl and 2-methylvinyl group.

R,6,1(17,■?,8,Rp%R110,)(+
2.1%+3, l(, l 4 and R15t; i, cycloalkyl group such as cyclopentyl group, cyclohexyl group, cycloheptyl group or cyclooctyl group.

Possible examples of cycloalkylalkyl radicals R7 are cyclohexylmethyl, cyclopentylethyl and 3-cyclohexylpropyl.

The γ-aryl group l (β, R7, R8 and the radicals can be a phenyl group or a naphthyl group. Possible examples of a phenyl or phenylalkyl group R9 substituted with OH and an alkyl group are 4-hydroxy-3 , 5-di-tert phthyl phenol group, A-hydroxy-3-methyl-5-
Tertiary methylbenzyl group, 3-hydroxy-tert-butylbenzyl group and 2-(1-hydroxy-3,5-di-tert-butylphenyl)-ethyl group and monopropyl group.

C7-C12 alkylaryl group Rρ, W
and T(7 possible examples are tolylxylyl, 4-butylphenyl, 4-methyl-1-naphthyl, and 3-ethylephenyl. Phenylalkyl group R.6. R?%R8・R9・1(,10,)(,!
4 and 1 (possible examples of 15 are - benzyl group - 2-phenylethyl group, 2-phenylpropyl group, 6-phenylpropyl M, A-phenylbutyl group and 4-methylbenzyl group O having 2 carbon atoms) Possible examples of from 1 to 10 alkanoyl radicals 1 (, 14) are acetyl, propionyl, butyryl/hexanoyl, α,α-dimethylpropionyl, octanoyl and decanoyl groups. (7) When 2 is a 5- to 7-membered ring, this can be, for example, a pyrrolidine, piperidine, morpholine t*-u, /l-alkylpiperazine ring.

R12 and 1 (13 together with the bonded carbon atom is a cycloalkane 1 or an alkylcycloalkanthane,
Cyclohexane, mono- or dimethylcyclohexane, ethylcyclopentane, cyclooctane can be a cyclododecane ring.

Possible examples of divalent radicals 11,4 representing aliphatic diisocyanates are di-, tri-, tetra-, hexa-octa-
, deca- and dodeca-methylene groups. Groups representing cycloaliphatic diisocyanates IL4 (7) oT functional examples (d, 1,4-cyclohexylene group, a -, t
Chill-'. , 3-cyclohexylene a, group: and the following formula: (wherein 11(, +9 is H%CH3'-!i or C2H
, and R,20 +. :t 11-+ or a group represented by C[(, suffix). Aromatic size or aromatic fat. Group R representing aliphatic diisocyanate
Possible examples of 4 are 1,4-' phenylene group, 1,3-
Phenylene group, 2.4-)rylene group, 2,6-tolylene group, 1,4-naphthylev group, '. 5-f ethylene group, A
, A'-diphenylene group and the following formula: 1(+9 1(,201(,191%20).

The trivalent group R4 representing triisocyanate is an aliphatic group,
It can be a cycloaliphatic or aromatic-aliphatic group. For example, it is a group represented by the following formula: %formula%) ) ).

When n represents the number 2, H4 is preferably 2 to 1.
divalent saturated, fI]Ii'rf aliphatic radicals having 6 carbon atoms, divalent cycloaliphatic radicals having 5 to 20 carbon atoms or divalent cyclic aliphatic radicals having 6 to 20 carbon atoms; aromatic 1 represents an aromatic-aliphatic group; 12, when n represents the number 3, 1 (, 4 preferably represents a trivalent aromatic-aliphatic group having 10 to 30 carbon atoms; represent.

A preferred compound represented by formula 1 is one in which R1 represents a hydrogen atom, and ? , a derivative of 2,6,6-titramethylbiperidine.

Other preferable compounds represented by formula 1 are those in which II represents a hydrogen atom] ~.
-I2COOr(6, -CI(2CH.

-N(rL')-CO-R,8,0-CO-R,9
, -N (R,?) -Co-ORIO Katsutake Ichi-
C0-N (117) 2, and H63 represents a hydrogen atom, or R2 and 1shi3 together represent 〇- or a group represented by the formula ■, II, ■ or V, and n is When representing the number 2, R4 has 2 to 1 carbon atoms;
The alkylene group of 2 is a phenylene group, a naphthalene group, a tolylene group or the following formula: %Formula% (In the formula, R119 represents a hydrogen atom, a methyl group and an ethyl group) 7, and I and 0 are hydrogen atoms and methyl (represents a group) represents a group represented by 17, and when n represents a number of 3, R4 is the following formula.

17. 1ts is an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, or pe.i x5 m
, :tl: Zu-AA+ J-1+ -R6 represents an alkyl group having 1 to 4 carbon atoms or a cyclohexyl group 7, W is an alkyl group having 1 to 12 carbon atoms, a cyclohexyl group, an allyl group or a phenyl group represents TI% and 119-/p alkyl group having 1 to 1712 carbon atoms (, alkenyl group having 2 to 3 carbon atoms,
Phenyl group, benzylgt*-u cyclohexyAI group, Table-b l/, so(7te1(, IO represents a phenyl group in alkyl group 1 having 1 to 12 carbon atoms, Formula 1 An example of a specific compound represented by the formula I is one represented by the following formula. Accordingly, the present invention also provides compounds of the formula (1): (wherein R1, R2 and R3 have the above meanings).

) with a diisocyanate or triisocyanate represented by the formula ■: R4(NGO)n (wherein n and R4 have the above meanings);
-20°C to +50°C preferably -50°C in an inert solvent
The present invention relates to a process for producing a compound represented by formula (2), which comprises reacting the compound represented by formula (1) at a molar ratio of n moles to 1 mole of the compound represented by formula (1) at a temperature of 0.degree. C. to +30.degree.

Particularly suitable inert solvents are hydrocarbons such as pentane, hexane, heptane, ligroin, benzine, cyclohexane, benzene, toluene and xylene, and ethers such as diethyl ether, diinoprobyl ether, tetrahydrofuran, dioxane and 1,2-dimethoxyethane. It is.

It is advantageous to start with a solution of the compound of formula (1) and add the solution of the compound of formula (1) while stirring and cooling. The temperature of the reaction mixture should thereby be kept below 50°C, preferably below 60°C.

2 mol of the compound of formula (1) are used per mol of diisocyanate. 3 mol of the compound of formula (1) are used per mol of triisocyanate. The reaction can be accelerated by adding a catalytic amount of a base soluble in the organic solvent. Examples are 1,4-diazabicyclo(2,2,2)octane and 1,8-diazabicyclo[5-4,O]undec-7-nintheal.

However, such a catalyst is not necessary.

The resulting product can either precipitate directly in crystalline form from the reaction solution or can be crystallized by cooling. Alternatively, some or all of the solvent may be distilled off without stirring, and the product may then be crystallized by cooling. In this way the product is obtained in high purity. Even though by-products may be produced, the desired 1-carbamyl compound can be obtained in high yield at low temperatures. This shows the surprising selectivity of this method. For example, if the diisocyanate contains 2 moles of 4-hydroxy-ζ2
．． When reacting with 6.6-titramethylpiperidine according to the method of the invention at room temperature (20-25°C), a 1-carbamyl compound of the following formula is formed in high yield. On the other hand, a 4-carbamyloxy compound is easily produced by a known method under heating (reflux, toluene).

The compounds of the formula I can be used as stabilizers for photosensitive organic materials, such as coating materials for cosmetic heavy duty or color photography, in particular as stabilizers for organic polymers. In addition to the significant photostabilizing effect, the compounds of formula 1 also provide certain stabilizing effects against thermal and oxidative aging of the polymer. Examples of such polymers are listed below.

(I+ Polymers obtained from monoolefins and diolefins, such as polyethylene (optionally crosslinked), polypropylene, polyisobutylene, polybutylene
1-ene, polymethylpent-1-ene, polyinobrene or polybutadiene, and also polymers of cycloolefins such as cyclopentene or norbornene.

f21 (Mixtures of the polymers listed in 11, for example mixtures of polypropylene and polyethylene fibers or polyinobutylene.

(3) Copolymers of monoolefins or diolefins with each other or with other vinyl monomers, e.g. t is ethylene/propynone copolymer, propylene/propylene-1-
ene copolymer, propylene/isobutylene copolymer, ethylene/phth-1-ene copolymer, fluoropylene/
butadiene copolymer, isobutylene/isoprene copolymer, ethylene/alkyl acrylate copolymer,
Ethylene/alkyl methacrylate copolymers, ethylene/vinyl acetate copolymers and ethylene/acrylic acid copolymers and their salts (ionomers), and terpolymers of ethylene with propylene and dienes such as hegisadiene, dicyclopentadiene or ethylidene norbornene.

(4) Polystyrene (5) Copolymers of styrene or a-methylstyrene with diene or acrylic acid derivatives, such as styrene/butadiene, styrene/acrylonitrile, styrene/ethyl methacrylate, styrene/phthadiene/ethyl acetate and styrene/acrylonitrile/ Methyl acrylate; high impact strength mixtures obtained from styrene copolymers and other polymers such as polyacrylates, diene polymers or ethylene/propylene/di-terpolymers: (-1, block copolymers of styrene, e.g. evastyrene/butadiene/styrene, Styrene/Isoprene/
Styrene/ethylene-butylene/styrene matahastyrene/ethylene-propylene/styrene.

(6) Graft copolymers of styrene, such as polybutadiene with styrene attached, polybutadiene with styrene and acrylonitrile, polybutadiene with styrene and maleic anhydride, polybutadiene with styrene and alkyl acrylate or alkyl methacrylate. , ethylene/propylene/genterpolymer with styrene and acrylonitrile, polyalkyl acrylate or polyalkyl methacrylate with styrene and acrylonitrile, acrylate/butadiene I copolymer with styrene and acrylonitrile, and these and 15)
copolymers mentioned above, such as the so-called ABS, MBS,
Mixtures with what are known as ASA or AES polymers.

(7) Halogen-containing polymers, such as polychloroprene, chlorinated rubber, chlorinated or chlorinated sulfonated polyethylene and epichlorohydrin homopolymers and copolymers, and especially polymers consisting of halogen-containing vinyl compounds, such as polyvinyl chloride, polyvinylitine chloride, poly Vinyl fluoride and polyvinylidene fluoride; and copolymers thereof such as vinyl chloride/vinylidene chloride copolymers, pi=# chloride/vinyl acetate copolymers and vinylidene chloride/vinylidene acetate copolymers.

(81G, Polymers derived from β-unsaturated acids and their derivatives, such as polyacrylates and polymethacrylates, and polyacrylamides and polyacrylonitrile.

(9) Copolymers of the monomers mentioned in (8) or with other unsaturated monomers, such as acrylonitrile/butadiene copolymers, acrylonitrile/alkyl acrylate copolymers, acrylonitrile/alkoxyalkyl acrylate copolymers, acrylonitrile/vinyl chloride copolymers and acrylonitrile/alkyl Methacrylate/butadiene terpolymer.

0e Polymers derived from unsaturated alcohols and amines or their acyl derivatives or acetals, such as polyvinyl alcohol, polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinyl maleate, polyvinyl butyral, polyallyl phthalate and polyallyl melamine.

α1) Homopolymers and copolymers of cyclic ethers,
For example, copolymers of polyalkylene glycols, polyethylene oxides, polypropylene oxides and bisglycidyl ethers.

(i″3 Polyacetals, such as polyoxymethylene, and polyoxymethylene containing ethylene oxide as a comonomer.

(13) Polyphenylene oxide and polyphenylene sulfide.

aa Polyurethanes obtained from polyethers and polybutadienes having a hydroxyl group on one end and aliphatic or aromatic polyisocyanates on the other hand, and their intermediates (polyisocyanates, polyols, prepolymers).

0 polyamides and copolyamides obtained from diamines and dicarboxylic acids and/or from aminocarboxylic acids or corresponding lactams, such as polyamide 4,
Polyamide 6, polyamide 6.6% polyamide 6.10
．． Polyamide 11, Polyamide 12, Poly-2,4゜4
- Trimethyl-hexamethylene-terephthalamide and poly-m-7 enylene-isophthalamide and their copolymers with polyethers, such as copolymers with polyethylene glycol, polypropylene glycol or polytetramethylene glycol.

(11 Polyurea, polyimide and polyamide-imide.

0η Polyesters derived from dicarboxylic acids and diols and/or polyesters derived from hydroxycarboxylic acids or corresponding lactones, such as polyethylene terephthalate, polybutylene terephthalate, poly-14-dimethylolcyclohexane terephthalate, poly-(2,2 - Block polyether-esters obtained from bis(4-hydroxyphenyl)propane-terephthalate and polyhydroxybenzoate, as well as hydroxyl-terminated polyethers, dialcohols and dicarboxylic acids.

0ki polycarbonate.

■ Polysulfone and polyether-sulfone.

Crosslinked polymers obtained from aldehydes on the one hand and phenols, urinary esters, and melamines on the other, such as pheno-φ formaldehyde resins, urinary thymurimaldehyde resins and melamine formaldehyde resins.

(El) Drying and non-drying alkyd resins.

(e) An unsaturated polyester resin obtained from a copolyester of a saturated or unsaturated dicarboxylic acid and a polyhydric alcohol using a vinyl compound as a crosslinking agent, and a low flammable halogen-containing modified resin thereof.

(c) Crosslinkable acrylic resins obtained from substituted acrylates, such as epoxy acrylates, urethane-acrylates or polyester acrylates.

(Foundation) Alkyd resins, polyester resins and acrylate resins crosslinked with melamine resins, urea resins, polyisocyanates or epoxy resins.

(c) Crosslinked epoxy resin obtained from polyepoxide.

(e) Natural polymers such as cellulose, natural rubber, and gelatin, and their derivatives chemically modified by polymer homologs, such as cellulose acetate, cellulose propionate, and cellulose ethers such as cellulose butyrate and methyl cellulose. .

Stabilization of surface coating resins such as acrylics, acrylics and polyester resins is particularly important, especially when these resins are used for acid-catalyzed varnishes.

The stabilizer according to the present invention can be used to stabilize the material to be stabilized.
．． It is added to the polymer at a concentration of 0.01 to 4.0% by weight. Preferably 01 to 2 based on the material to be stabilized.
% of the compound by weight is mixed into this material.

The compounds can be mixed before, during or after polymerization. For example, before or during molding, the compound, if desired together with other additives, is mixed into the melt by methods customary in the art. In the case of varnishes, the compound is preferably added to the varnish solution before application of the varnish.

Stabilizers can also be added in the form of masterbatches. Masterbatches contain these compounds, for example, in a concentration of 2.5 to 255% by weight, based on the polymer to be stabilized.

Besides the compounds of formula I, other known stabilizers can also be added to the polymers. Stiffeners are, for example, antioxidants, light stabilizers or metal deactivators, or costabilizers, such as costabilizers of the phosphite type. Other additives customary in plastics technology, such as flame retardants, antistatic agents, plasticizers, lubricants, adhesives,
Pigments, reinforcing agents or fillers can also be added.

Known stabilizers may also be used to produce a synergistic effect. This effect often occurs when other light stabilizers or organic phosphites are used. The additional use of antioxidants is particularly important for stabilizing polyolefins.

The invention therefore also provides compounds of formula I with 0.1
It relates to organic polymers which are stabilized by the addition of 4-fold fk and which, if desired, can also contain other known and conventional additives. Stabilized glasstex can therefore be used in a variety of forms, for example as a binder for films, fibers, tapes, profiles or, in particular, varnishes.

METHODS OF MAKING AND USE OF THE COMPOUNDS OF THE INVENTION.

This will be explained in further detail in the following examples. Among these examples.

"Parts" and "ch" represent "parts by weight" and "% by weight." The temperatures given are in degrees Celsius.

In these examples, formula 1: represents a 2,2,6,6-thitrametherbiperidine group. Example 1 A solution of hexamethylene diisocyanate 16.8.9 (0.1 mol) in tetrahydrofuran Sod of 314 g of 4-hydroxy-2,2,46-titramethylhyheridine in 300 Mt of anhydrous tetrahydrofuran (
2 mol) of α2 mol) regularly dropwise over a period of 7 hours at 22-25°C. Further stirring is continued at room temperature overnight to form a thick white suspension of the reaction product.

The reaction product was filtered off, washed thoroughly with cold tetrahydrofuran, filtered off with strong suction and dried at room temperature under high vacuum. The dicarbamyl compound thus obtained is
The analytically pure 0''H-NM spectrum (ODOI, ) with a melting point of 145-146° was in good agreement with the given structure.

02 H5ON, 0. Calculated value: 064.691-T
10.44 N11.61% (482,7) Actual value:
064.5 [10,6N11.8 t The compounds listed in Table 1 were similarly prepared from polyalkylpiperidines and diisocyanates.

Example 2 100 parts of polypropylene powder (Mol)
en) % 41 chore grade, Monte Giso 7 (Mon-t
edison)) was mixed with 12 parts of octadecyl p-(
3,5-di-tert-butyl-4-hydroxyphenyl)-
The mixture was homogenized for 10 minutes at 200 DEG C. in a Gravender Plastograph with O, 1 part of calcium stearin and 0.25 parts of a stabilizer from Table 1. The mass thus obtained was removed from the kneader as soon as possible and pressed into 2-3312I planks in a toggle press.

Pieces of the resulting blank were cut and pressed between two pieces of high gloss hard aluminum foil at 260°C for 6 minutes using a hydraulic laboratory press to obtain a 0.11111 thick film. The film was immediately cooled in cold water. This film was now punched out, shaped and exposed in a Xenotest 1200. These specimens were taken out from the exposure apparatus at regular time intervals, and their carbonyl content was measured using an IR spectrophotometer (1.55-85 in i''L light exposure).
The increase in carbonyl absorbance of ff was taken as a measure of photooxidative degradation of the polymer (L, Blaban et al. J, Poly-
mer Sci, Part O; Volume 22 (1969
1059-1071). Experience has shown that this measure reveals changes in the mechanical properties of the polymer.

The time taken to reach a carbonyl absorbance of about 0.3, the point at which the control film became brittle, was a measure of the stabilizing effect.

Continuing from page 1 ■Int, C1,' Identification symbol Internal office reference number 496:
10)

Claims (1)

[Claims] tll Formula I: (In the formula, n represents the number of two straddles, 11 and ' hydrogen D) represents an L atom or an alkyl group having 1 to 4 carbon atoms, and ■C represents Hydrogen 1fJt child, -〇11, -oxr, -C00
R6, -needle x,, cooIr, -C1l,, CN, ~C
N, -N (I(,7)2, -CO-N (R7a)
2,-CH2CH2N (R7)2,-N(1,?a)
-Co-R', -0-CO-170, -0CH2CI-
12-CN. -N (R7a)-Co-0-R10, 0-CO-□
It, ' n, -0-Co-N (R"') 2 or group: itF represents a hydrogen atom, or R and l also 3 become sticky and 0-1NC-CH- or the following formula ■ , ■
, ■, ■ or ■: ■■ ■■ I(, +2 ■ represents a group represented by R4 is an aliphatic, cycloaliphatic, aromatic or aromatic-aliphatic diisocyanate or n-
represents a valent group, T4' is an alkyl group having 1 to 12 carbon atoms, oxaalkyl group having 6 to 14 carbon atoms;
II (, C 3 -C 5 alkenylbargyl group, benzyl group or -(CH2CH20 )
pH group (in the group, p represents a number from 1 to 10)
represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, and 5 carbon atoms.
cycloalkyl group having 6 to 8 carbon atoms, 6 to 10 carbon atoms
represents an aryl group having 7 to 12 carbon atoms, an alkylaryl group having 7 to 12 carbon atoms, a phenylalkyl group having 7 to 712 carbon atoms, or a group represented by the formula M: where R7 is an alkyl group having 1 to 18 carbon atoms, a carbon atom Oxaalkyl group having 2 to 14 carbon atoms, alkenyl group having 3 to 5 carbon atoms, cycloalkyl group having 5 to 8 carbon atoms, phenylalkyl group having 7 to 12 carbon atoms, aryl having 6 to 10 carbon atoms group, C2-C4 hydroxyalkyl group or C7
represents from 1 to 10 cycloalkyl-alkyl groups,
Alternatively, the two R7 groups together with the nitrogen atom to which they are bonded represent a 5- to 7-membered ring, Baa represents a hydrogen atom or one of the meanings of It', and R8 represents a carbon an alkyl group having 1 to 12 carbon atoms, an oxaargyl group having 3 to 14 carbon atoms, an alkyl group having 2 to 14 carbon atoms substituted with -COOII or -coo (an alkyl group having 1 to 4 carbon atoms); ,
C2-C5 alkenyl group, C5-C8 cycloalkyl group, C7-C12 phenylalkyl group, C6-C10 aryl group or C7-C17 alkyl group represents an aryl group, l (O is an alkyl group having 1 to 18 carbon atoms, an oxaalkyl group having 3 to 14 carbon atoms, -
C2-C14 alkyl group substituted with COOH or -COO (C1-C4 alkyl group), C2-C5 alknyl group, C5-C8 cycloalkyl group C 6 -C 10 aryl, C 7 -C 12 phenylalkyl, C 7 -C 12 alkylaryl or OH and 1 - 3 C 1
represents a phenyl group substituted with an alkyl group having 7 to 4 carbon atoms or a phenylalkyl group having 7 to 10 carbon atoms; )+IO represents an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms; 5 to 8 cycloalkyl group, phenyl group or carbon number 7
1 to 12 phenylalkyl groups; ILll represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; represents a cycloalkyl group or a benzyl group, and 1(, +3 represents a C1-C12 alkyl group, a C5-8 cycloalkyl group or a phenyl group, or ■+12 and I(, +3 represents a cycloalkane or alkylcycloalkane ring having 6 or more carbon atoms (-14) formed together with the carbon atoms to which they are bonded, and 414 represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. , alkenyl group having 3 to 5 carbon atoms, cycloalkyl group having 5 to 8 carbon atoms, hydroxyalkyl group having 2 to 4 carbon atoms, alkanoyl group having 2 to 10 carbon atoms, benzoyl group, carbon atom number 7 to 1
2 represents a phenylalkyl group or an R-NH-CO- group (in the group, ``mo'' represents an alkyl group having 1 to 8 carbon atoms or a phenyl group), RI+5 is a hydrogen atom, and RI+5 is a hydrogen atom, and RI+5 is a hydrogen atom, an alkyl group having 6 to 5 carbon atoms, an alkenyl group having 6 to 5 carbon atoms, a hydroxyalkyl group having 2 to 4 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, a phenylalkyl group having 1 to 12 carbon atoms or a glycidyl group; R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R represents a hydrogen atom, a methyl group, an ethyl group, or a hydroxymethyl group; and R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; group, allyl group, benzyl group, acetyl group or acryloyl group. ). (2) In formula I, n represents the number 2, and I
divalent saturated I in which L4 has 2 to 16 carbon atoms
N represents a divalent cycloaliphatic radical having 5 to 20 carbon atoms; or VJ represents a divalent aromatic aromatic-aliphatic radical having 6 to 20 carbon atoms;
Or n represents the number 6 and W is 10 to 60
A compound according to claim 1 representing a trivalent aromatic-aliphatic group having 5 carbon atoms. (3) The compound according to claim 1, wherein in formula (1), 1σ represents a hydrogen atom. (4) In formula I, R1 represents a hydrogen atom, and R2 is -OH, -OR', -CM2COOR', -CH
2CH. -N (R') -CO-R,8,0-CO-I(,
', -N (I(7)-Co -o alo or 10-CO-N (R')2, and R3 represents a hydrogen atom or ■σ and 1 di together represents O2 or a group represented by the formula ■, ■, ■ or V, and when n represents the number 2, R' has a carbon atom number of 2 to 1;
2 alkylene group, phenylene group, naphthylene group, tolylene group or the following formula: (In the formula, 2 represents a hydrogen atom, a methyl group or an ethyl group, and 1 (20 represents a hydrogen atom or a methyl group.) and when n represents the number 3, It' represents a group represented by the following formula; R' is an alkyl group having 1 to 12 carbon atoms, It represents an alkenyl group or a benzyl group, It' represents an alkyl group having 1 to 4 carbon atoms or a cyclohexyl group, and (2) more represents an alkyl group having 1 to 12 carbon atoms, a cyclohexyl group, an allyl group, or a phenyl group. ＼ R' and R9 represent an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 3 carbon atoms 11., a phenyl group, a benzyl group, or a cyclohexyl group 7
, and +t10 represents an alkyl group having 1 to 12 carbon atoms or a phenyl group. (5) Formula ■: (In the formula, ltl, R2 and ■ have the following meanings.) A compound represented by the formula ■: IC(NCO). ■ A diisocyanate or triincyanate represented by (in the formula, n and R' have the following meanings);
-20°C to +50°C preferably -50°C in an inert solvent
Formula I, consisting of reacting at a temperature between 1 mol and 1 mol of the compound represented by the formula 1 at a temperature of 1 mol of the compound represented by the formula 1 to n mol of the compound represented by the formula R' represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
-CI(2COOR0, -CH,,CN, -CN,
-N (I't7)2, CON(R7a)2, CH2C
H2N(R7)2, N (R?a >-Co-I(,
', -0-CO-R', -0CH2CH,, -CN. -N (R7a) -CO-0-R10, -0-CO-
0-It", -0-Co-N (R7a)2-d 7'
(id, M: ■♂ represents hydrogen/j (child, but rurui is It2 and ■mo' together are 〇2, NC-C
l-]-segmentation is expressed as HlIt/V■. 7. I:f: Represents IC (17 is an aliphatic, cycloaliphatic, aromatic or aromatic-aliphatic diisocyanate or trigyl group, an alkenyl group having 3 to 5 carbon atoms, a propargyl group,
represents a benzyl group or -(CH2C1(20), H group (in the group, p represents a number of 1 to 1°), R6 is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, 3 carbon atoms alkyl having 5 to 5 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, aryl having 6 to 10 carbon atoms 7.1-1 alkylaryl having 7 to 12 carbon atoms, cycloalkyl having 5 to 8 carbon atoms; It represents a phenylalkyl group or a group represented by 2:, where It7 is an alkyl group having 1 to 18 carbon atoms, an oxaalkyl group having 2 to 14 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, cycloalkyl group having 5 to 8 atoms, phenylalkyl group having 7 to 12 carbon atoms, aryl group having 6 to 10 carbon atoms, carbon JM
represents a hydroxyalkyl group having 2 to 4 molecules or a cycloalkyl-alkyl group having 7 to 10 carbon atoms, or 2 R? The groups together with the nitrogen atom to which they are bonded represent a 5- to 7-membered ring, It
represents a hydrogen atom or one meaning of LL', It8 is an argyl group having 1 to 12 carbon atoms, a carbon atom lii, an oxaalkyl group having 5 to 14 atoms, -COO
C2-C14 alkyl group substituted with H or 1000 (C1-C4 alkyl group), C2-C5 alkenyl group, C5-C8 cycloalkyl group radical, 7 to 1 carbon atoms
2 represents a phenylalkyl group, an aryl group having 6 to 10 carbon atoms, or an alkylaryl group having 7 to 17 carbon atoms, and 149 represents an alkyl group having 1 to 18 carbon atoms, an oxaalkyl group having 6 to 14 carbon atoms; 2 to 14 carbon atoms substituted with -COOH or -Coo (alkyl group of 1 to 4 carbon atoms)
an argyl group, a C2-C5 alkenyl group,
cycloalkyl group having 5 to 8 carbon atoms, aryl group having 6 to 10 carbon atoms, phenylalkyl group having 7 to 12 carbon atoms, alkylaryl group having 7 to 12 carbon atoms or OH and 1 to 6 represents a phenyl group or a phenylalkyl group having 7 to 10 carbon atoms substituted with an alkyl group having 1 to 4 carbon atoms, fL'' is a carbon atom & an alkyl group having 1 to 12 carbon atoms, represents an alkenyl group, 1, a cycloalkyl group having 5 to 8 carbon atoms, a phenyl group, or a phenylalkyl group having 7 to 12 carbon atoms, and nl 1 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; In the expression, 1, t, +2 represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms (, a cycloargyl group having 5 to 8 carbon atoms, or a benzyl group, and p-, 1g, +, 7 - !″Number of oligonucleotide atoms is 1 or 1
2 represents an alkyl group, a cycloalkyl group having 5 to 8 carbon atoms, or a phenyl group; Ncroalkane mater represents an alkylnchloroalkane ring, R.14 is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 6 to 5 carbon atoms, a cycloalkane group having 5 to 8 carbon atoms. Alkyl i7'4, hydroxyargyl group having 2 to 4 carbon atoms, alkanoyl group having 2 to 1 o carbon atoms, benzoyl group, 7 carbon atoms
to 12 phenylargyl groups or I(, --NH
-CO- group (in L, It represents an argyl group having 1 to 8 carbon atoms (represents a phenyl group), R1!t is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, C377-C5 alkenyl, C2-C4 hydroxyalkyl, C5-C8 cycloalkyl, C1-C1
2 represents a phenylalkyl group or a glycidyl group, R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, it I7 represents a hydrogen atom, a methyl group, an ethyl group, or a hydroxymethyl group, and B+8 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an allyl group, a benzyl group, an acetyl group or an acryloyl group. ) A method for producing a compound represented by rl. (6) Formula I as a stabilizer for photosensitive materials: (where n
represents the number 2 or 3, I (1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, W represents a hydrogen atom, -OH,0T-L', -COOi(,'
, -CI-12COOR', -CH2CN, -CN,
-N (R'), -CO-N (It7a)2,
-CH,CH2N(R7)2, -N(R,”)-〇〇-
IL', -0-Co-R", -0CI-12CH
2-CN. -N (■+7a) -co-o-rtlo, -0-C
o-0-R”, 0-CO-N (R7a)21 fc
l”i group 'R3 represents a hydrogen atom, or R
2 and W together represent 0-1NC-CH= or a group represented by the following formula ■, ■, ■, ■ or ■: l DI ■ v tl 2 ■, I(,' is aliphatic, cyclic represents an n-valent group of aliphatic, aromatic or aromatic-aliphatic diisocyanate or triisocyanate, R5 is an alkyl group having 1 to 12 carbon atoms, an oxaalkyl group having 3 to 14 carbon atoms, or an oxaalkyl group having 3 to 14 carbon atoms; 3 to 5 alkenyl group, glopargyl group, benzyl group or -(CH,0H20), n group (
In the group, p represents a number from 1 to 1o. ), R' represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, or a 5 carbon atom
-8 cycloalkyl group, having 6 -1 o carbon atoms
represents an aryl group having 7 to 12 carbon atoms, an alkylaryl group having 7 to 12 carbon atoms; , oxaalkyl group having 2 to 14 carbon atoms, alkenyl group having 3 to 5 carbon atoms, cycloalkyl group having 5 to 8 carbon atoms, phenylalkyl group having 7 to 12 carbon atoms, 6 to 10 carbon atoms aryl group, C2-C4 hydroxyalkyl group or C7
represents from 1 to 10 cycloalkyl-alkyl groups,
Alternatively, the two R' groups together with the nitrogen atom to which they are bonded represent a 5- to 7-membered ring, R7a represents a hydrogen atom or has one meaning of IC, and It' is an alkyl group having 1 to 12 carbon atoms, an oxaalkyl group having 3 to 14 carbon atoms, -COOH or -COO (alkyl group having 1 to 4 carbon atoms), and li? F-substituted carbon-4 alkyl group having 2 to 14 atoms, alkenyl group having 2 to 5 carbon atoms, carbon atom?
i15 to 8 cycloalkyl group, C7 to C12 phenylalkyl group, C6 to C10
represents an aryl group or an alkylaryl group having 7 to 17 carbon atoms, and each carbon atom I! i3 to 14 oxaalkyl group, C2 to C14 alkyl group substituted with -COOH or -C00 (C1 to C4 alkyl group), C2 to C5 alkenyl group, carbon atom cycloalkyl group having 5 to 8 carbon atoms, aryl group having 6 to 10 carbon atoms, 7 carbon atoms
1 to 12 phenylalkyl groups, C7 to C12 alkylaryl groups or OH and 1 to 6
phenyl or phenylalkyl group having 7 to 10 carbon atoms substituted with ttZ-substituted alkyl group having 1 to 4 carbon atoms; R'' is an alkyl group having 1 to 12 carbon atoms; 5 alkenyl group, C5-C8 cycloalkyl group, phenyl!!i or C7
to 12 phenylalkyl groups, IL'1 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, IL is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or a phenylalkyl group having 5 to 8 carbon atoms. represents a cycloalkyl group or a benzyl group, and R represents a C1-C12 alkyl group, a C5-8 cycloalkyl group or a phenyl group, or R'' and R13 are bonded together. 6 to 14 carbon atoms formed by force together with carbon atoms
represents a cycloalkane or alkylcycloalkane ring, R is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms,
C5-C5 alkenyl, C5-C8 cycloalkyl, C2-C4 hydroxyalkyl, C2-C10 alkanoyl, benzoyl, C7-C8 12 phenylalkyl groups or R-NH-CO- groups (among the groups, R
represents an alkyl group having 1 to 8 carbon atoms or a phenyl group. ), R'' represents a hydrogen atom, an argyl group having 1 to 18 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, or a C 2
to 4 hydroxyalkyl group, C5 to C8 cycloalkyl group, C1 to C12 phenylalkyl group or glycidyl group, rt, +6 Ff, hydrogen atom or C1 to C4 alkyl group; I't'7 represents a hydrogen atom, a methyl group, an ethyl group or a hydroxymethyl group, and R'' represents a hydrogen atom, a C1-C4 argyl group, an allyl group, a benzyl group, an acetyl group (or represents an acryloyl group). (7) The method according to claim 6, in which the compound is used as a stabilizer for an organic polymer. (8) As a stabilizer, a compound represented by the formula ■: (in the formula , n represents the number of 2 and 3, R' represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R2 is a hydrogen atom, -0R1-OR', -coortb'
, -C11□COO■also 6, -cH2cN , -CN,
-N (IC7)2, -CO-N (R"')2, -
CH2C112N (IC7)2, -N(R7a)-C
OR,8, -0-Co-R9, -0CH2CI(2-
C.N. -N (](,7a)-CO-0-[10,-o-co
-o-rt'', -0-CC)-N (also I)2 or the group: 0 0 W represents a hydrogen atom, or R2 and R3 together represent 0-1NC-CH= or the following formula ■ ,■,■,
■ or ■: ■ ■ IV V ■ represents a group represented by
represents a valent group, IC5 is an alkyl group having 1 to 12 carbon atoms, an oxaalkyl group having 6 to 14 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, propalkyl μ, a benzyl group or -(CH2CH20), II group (
In the group, p represents a number from 1 to 10. ), R6 is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an alknyl group having 6 to 5 carbon atoms, and 5 carbon atoms.
-8 cycloalkyl group, having 6 -10 carbon atoms
represents an aryl group having 7 to 12 carbon atoms, an alkylaryl group having 7 to 12 carbon atoms, a phenylalkyl group having 7 to 12 carbon atoms, or a group represented by 2:, where IC7 represents an alkyl group having 1 to 18 carbon atoms, a carbon atom Oxaalkyl group of number 2 to 14, carbon atom vI5
alkenyl group having 5 to 5 carbon atoms, cycloalkyl group having 5 to 8 carbon atoms, phenylalkyl group having 7 to 12 carbon atoms, aryl group having 6 to 10 carbon atoms, hydroxyalkyl group having 2 to 4 carbon atoms, or represents a cycloalkyl-alkyl group having 7 to 10 carbon atoms, or two 1 moa groups together with the nitrogen atoms to which they are bonded represent a 5- to 7-membered ring; represents a hydrogen atom or has one of the meanings of R7, R8 is an alkyl group having 1 to 12 carbon atoms, an oxaalkyl group having 6 to 14 carbon atoms, -COOII or -C00 (having 1 to 14 carbon atoms) C2-C14 alkyl group, C2-C5 alkenyl group, C5-C8 cycloalkyl group, C7-C12 phenylalkyl group substituted with C4 alkyl group) , represents an aryl group having 6 to 10 carbon atoms or an alkylaryl group having 7 to 17 carbon atoms, and LtO is argyl having 1 to 18 carbon atoms.
, 1, oxaalkyl group having 3 to 14 carbon atoms, -
COOH or -C00 (alkyl group having 1 to 4 carbon atoms), alkyl group having 2 to 14 carbon atoms, alkenyl group having 2 to 5 carbon atoms, cycloalkyl group having 5 to 8 carbon atoms, Number of carbon atoms: 6
aryl of 1 to 10 carbon atoms, phenylalkyl of 7 to 12 carbon atoms, alkylaryl of 7 to 12 carbon atoms or phenyl substituted with OH and 1 to 3 carbon atoms of alkyl; phenylalkyl having 7 to 10 carbon atoms; Represents a phenyl group or a phenylalkyl group having 7 to 12 carbon atoms; ① represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; H represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms; , represents a C5-C8 cycloalkyl group or a benzyl group, and R13 represents a C1-C12 alkyl group, a C5-8 cycloalkyl group or a phenyl group, or R12 and Rr3 represents a cycloalkane neck or alkylcycloalkane ring having 6 to 14 carbon atoms formed together with the carbon atoms to which they are bonded; , C3-C5 alkenyl, C5-C8 cycloalkyl, C2-C4 hydroxyalkyl, C2-C10 alkanoyl, benzoyl, C7 or 1
2 phenylalkyl groups or 1(・-Nl(-Co-
represents a group (in the group, R represents an alkyl group having 1 to 8 carbon atoms or a phenyl group); 1mo15 is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an alkyl group having 3 to 5 carbon atoms; represents an alkenyl group, a hydroxyalkyl group having 2 to 4 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, a phenylalkyl group having 1 to 12 carbon atoms, or a glycidyl group, R16tj, a hydrogen atom or 1 carbon atom; )417 represents a hydrogen atom, methyl group, ethyl group or hydroxymethyl group, and I and 18 represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an allyl group, a benzyl group, Represents an acetyl group or an acryloyl group. ) at least one compound represented by 0.01 to 47
Organic polymer containing 1'j hj%. (9) The organic polymer according to claim 8 as a binder for varnish.